What is the seating like on the boat?

Seating is on cushions on the deck for a close-to-the-water experience; guests often sit together in small groups for views.

What should I wear aboard the Sunset Sail?

Dress comfortably with non-slip shoes (avoid heels), plus a light jacket or sweater for cooler breezes; bring sunscreen, a hat, and sunglasses for sunny days.

Will I get wet on the cruise?

Typically no—guests stay dry—but wind and sea spray can cause light dampness during certain conditions; a waterproof layer helps.

Are there restrooms on board?

Yes, there is a small restroom (head) on board, down a set of steps.

Do all ages require a ticket?

Yes, all ages require a ticket; no child or infant rate is offered as fares are per person.

Is the trip wheelchair accessible?

Not wheelchair accessible; there are steps to board and narrow walkways—contact the operator in advance if you have mobility concerns.

Sail the Stars & Stripes: Hilton Head Sunset Cruise on a Legendary America’s Cup 12-Meter

On Hilton Head Island, South Carolina, an evening aboard the Private Sunset Sail aboard Stars & Stripes turns a routine sunset into a maritime show. Meeting at 149 Lighthouse Rd. Hilton Head Island, SC 29928, guests board at the Harbour Town Pier and step onto a genuine America’s Cup 12-Meter once skippered by Dennis Connor. The boat squats low to the water, with cushions on deck and a close-to-water perspective that brings the Lowcountry’s salt marshes and barrier islands into intimate view. As you ease away from the pier, the route frames Daufuskie Island, Calibogue Sound, and the marshland channels that define this coastline. The area’s defining features are tidal salt marshes, winding creeks, and flat sandy spits—geology shaped by ebb and flow rather than elevation. Expect wide skies, long reflections on the water at low tide, and a shorebird chorus that includes pelicans and oystercatchers. Dolphins frequently quarter the bow, turning the sunset into an active marine theater. The experience balances participation and relaxation. Novices can simply sit and take the breeze; adventurous guests can join the crew to trim sails and learn basic helming. Drinks are available for purchase on board, which keeps things convivial without overwhelming the sea’s steady rhythms. Seating on cushions means a communal feel; restrooms are aboard below deck for convenience, reached by a short stair. Safety and access are straightforward but practical: there are steps to board and narrow walkways, so mobility needs should be considered ahead of time. The trip suits families, couples, and small groups—it's recommended for ages three and up—and accommodates up to 29 passengers, making it intimate enough to catch a private-moment vibe without feeling isolated. Beyond the immediate spectacle, this sail connects to local maritime history. The Stars & Stripes carries an America’s Cup pedigree and the memory of competitive sailing, which adds texture to a coastal sunset. Watching the sun slip behind Daufuskie Island with Harbour Town’s lighthouse silhouette nearby links natural beauty to human stories of navigation and competition. For travelers based on Hilton Head, this two-hour outing is an efficient evening cap: brief, scenic, and easy to fit into a day of golf, biking, or marsh exploration. It’s an especially good choice when the forecast promises clear skies and calm winds. The Private Sunset Sail is less a passive tour and more a coastal ritual—experienced aboard a piece of racing history and framed by the Lowcountry’s marshy edge. Reserve boarding 30 minutes before departure to settle in and choose a forward or aft view. Bring non-slip shoes and layers for cooling breezes; cameras benefit from a short monopod or steady hand to catch the evening light. Small groups can book privately for celebratory outings. Often.

About Vagabond Cruise

Vagabond Cruise operates a diverse fleet from Hilton Head Island, offering narrated wildlife excursions, specialty dining cruises, private charters, and seasonal holiday sailings. Flagship vessels include the Tammy Jane, Spirit of Harbour Town, Solaris, Vagabond, and the historic Stars & Stripes, each tailored for experiences ranging from two-hour crabbing and shrimping expeditions to multi-hour trips to Daufuskie Island and Savannah. Guests can choose guaranteed dolphin encounters on ocean and estuary cruises, relaxed sandbar sunbathing charters, intimate Solaris private charters for up to ten guests, or festive themed sailings such as fireworks dinners, holiday brunches, and the Gregg Russell Bubble Gum Cruise. Dining options feature Lowcountry menus and plated dinners crafted by award-winning chefs, buffet brunches, and specialty Gullah Geechee cuisine, with indoor climate-controlled cabins and open-air decks available. Educational offerings include narrated naturalist sunset dolphin cruises, stargazing sessions with “Bill the Sky Guy,” and paranormal ghost tours led by local experts. The company highlights hands-on marine experiences—baiting crab pots, hauling shrimp nets, and sorting fresh Carolina shrimp—designed for families and curious travelers. Safety and professional service are provided by experienced captains and trained crew, with full-service bars and private tables on select vessels. Vagabond Cruise partners with Sea Pines Resort for catering on exclusive Solaris charters and coordinates holiday events throughout the season. With a broad calendar of daily and special-event sailings, Vagabond Cruise delivers reliable, locally rooted maritime adventures across the Lowcountry. Bookings are available online with flexible options for groups, families, and private celebrations and seasonal themed departures.